Well, I just received a custom order from Alden: a 975 Longwing in #8 cordovan, but on the Plaza last, and with a single sole. I'm already in love with it.

Is there a reason why I shouldn't just order four or five more of exactly the same shoe? I would keep a pair of black captoes around for occasions when they're required. But so long as I'm comfortable wearing these Longwings on a day-to-day basis, even with business suits, is there anything I should fear other than boredom?

Many guys don't even bother to rotate, so I don't see a problem with sticking to one style. It's a bit "Monk"-ish, but whatever works for you. It's probably less eye-grabbing than rotating 40 pairs of high-end shoes, and, in that regard, might serve you well in a conservative industry.

Would you have all five pairs in rotation? I'd be cautious about stocking up for future use if only because of the possibility they might not fit 10 years down the line.

Although I would never do it, I always found it interesting to wear the same thing everyday! To have a closet full of the same suit, shirt, tie, and shoe. My friend wears all black everyday but in different ways. It has become his trademark and people love it! I am not sure wearing the same shoe is enough to make it intriguing though.

Although I would never do it, I always found it interesting to wear the same thing everyday! To have a closet full of the same suit, shirt, tie, and shoe. My friend wears all black everyday but in different ways. It has become his trademark and people love it! I am not sure wearing the same shoe is enough to make it intriguing though.

Although I would never do it, I always found it interesting to wear the same thing everyday! To have a closet full of the same suit, shirt, tie, and shoe. My friend wears all black everyday but in different ways. It has become his trademark and people love it! I am not sure wearing the same shoe is enough to make it intriguing though.

I know many people who wear the same outfit every day, except they only have one of each.